反应详情

温度

0 °C

Acetaldehyde (0.52 ml, 0.4 g, 9.08 mmol, 5 eq) was added to a stirred solution of tert-butyl 3-aminobenzylcarbamate (derived from 3-(aminomethyl)aniline (TCI America)) in 11 ml CH3CN/H2O (10:1) at 0° C. After 5 min NaBH3CN (0.3 g, 4.54 mmol, 2.5 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc and stirred at 0° C. for 5 min. The ice-bath was removed and the reaction was stirred at room temperature for 45 min. The solvent was removed in vacuo. The residue was diluted with saturated aqueous NaHCO3 and extracted with EtOAc (×2). The combined organics were washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.3875 g (1.4 mmol, 77% yield) of tert-butyl 3-(diethylamino)benzylcarbamate.

1. customThe ice-bath was removed
2. stirringthe reaction was stirred at room temperature for 45 min
3. customThe solvent was removed in vacuo
4. additionThe residue was diluted with saturated aqueous NaHCO3
5. extractionextracted with EtOAc (×2)
6. washThe combined organics were washed with water (×3), brine (×1)
7. dry with materialdried over Na2SO4
8. filtrationThe inorganics were filtered off
9. customthe solvent was removed in vacuo
10. customPurification via flash chromatography